5-Nitroso-2,4,6-pyrimidinetriamine → 2,4,7-Triamino-6-(2-chlorophenyl)pteridine

HRID 440890

Reaction equation

HRID 440890 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:9]=O)=[C:4]([NH2:11])[N:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]#[N:21].C[O-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]2[C:4](=[N:11][C:20]([NH2:21])=[C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[Cl:12])[N:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 705045-Nitroso-2,4,6-pyrimidinetriamineHCID 76112(o-Chlorophenyl)acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 152789352,4,7-Triamino-6-(2-chlorophenyl)pteridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.5 grams (0.010 mole) of 2,4,6-triamino-5-nitrosopyrimidine in 80 mL of N,N-dimethylformamide was heated to reflux, and 2.0 grams (0.01 3 mole) of 2-chlorophenylacetonitrile was added in one portion. Upon completion of addition, the reaction mixture was cooled, and 0.7 gram (0.013 mole) of sodium methoxide was added in one portion. The reaction mixture was again heated at reflux for 15 minutes. The reaction mixture was cooled in an ice-bath and then was filtered to collect a solid. The solid was slurried in diethyl ether and then was again collected by filtration, yielding, when dried, 2.5 grams of 2,4,7-triamino-6-(2-chlorophenyl)pteridine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto reflux
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was cooled
  4. temperatureThe reaction mixture was again heated
  5. temperatureat reflux for 15 minutes
  6. temperatureThe reaction mixture was cooled in an ice-bath
  7. filtrationwas filtered
  8. customto collect a solid
  9. filtrationwas again collected by filtration
  10. customyielding
  11. customwhen dried

Sources & evidence

ORD record
ord-026491380cda4feb8509110ad50d91ee
Source dataset
uspto-grants-1996_05
Patent number
US05521190

Linked notes

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